


In a Place of Gangs and Jazz

by BadassXxHoplessRomantic



Category: Supernatural
Genre: Al Capone (Big gang boss), Alternate Universe - Human, Alternate Universe- 1922 Chicago, F/M, Gen, Humor, Joe "King" Oliver and Creole band, Louis Armstrong, M/M, Mentions of other characters - Freeform, Multi, OC's - Freeform, Some angst, smut in later chapters, somewhat historical
Language: English
Status: In-Progress
Published: 2013-10-07
Updated: 2013-10-07
Packaged: 2017-12-28 16:03:11
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,224
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/993847
Author URL: https://archiveofourown.org/users/BadassXxHoplessRomantic/pseuds/BadassXxHoplessRomantic
Summary: <blockquote class="userstuff">
              <p>Castiel Novak and Dean Winchester are like two different species in Chicago of 1922. Castiel is stoic and a wealthy virgin, Dean is boisterous and poor and screwed anything with legs. Castiel didn't really like his life. All the money and power and expectations drive him insane. Dean likes his life. He and his surrogate family are happy, and he is content with his job. But when Castiel and Dean are forced by their respective family members to attend a Snob Party, they meet and both of their lives change drastically. Secrets from their pasts rear their ugly heads and they both question all that they've ever known and though. Conspiracies and temper's alike run high, and much is at stake. Gang bosses and jazz musicians litter the city. With homosexuality starting to be accepted as well as woman's rights, things in The Booming 20's are upside down. In a place of gangs and jazz, many things can happen. Both good and bad.</p>
            </blockquote>





	In a Place of Gangs and Jazz

**Author's Note:**

> I will finish what happens from the end of this chapter in chapter 2 from Dean's POV. Read notes at the ends please.

 

 

“Castiel Novak, you are going to attend this Gala and escort your sister. That is final.” Michael declared, settling back against his chair. Castiel huffed out an annoyed breath but didn’t argue further.

 

“Yes Michael.” Castiel grumbled out.

 

“Good. I advise you get ready for the gala. We leave in an hours’ time.” Castiel nodded then left his brothers office. He didn’t understand why he was being forced  to go to this Publicity Awards gala. It was basically a place for all of the higher-up’s to stick their noses higher than usual, no matter how they said it was a party in a Hero’s Honor.

 

Castiel didn’t really understand why _they_ had to go. Of all people. The Novak family was one of the most powerful families in the country, and even though this party was big, it wasn’t so important that it should capture their attention. Yet Michael was head set on going. The Novak family had always come from money. Castiel’s father, Christo Novak, and his uncle Zachariah had come from a wealthy English family. His mother, Eve Drago, came from a powerful and wealthy family of Italian nobles. Together his mother and father had three children. Their first child was Michael, who was born January 10, 1890 and now at the age of thirty-two. Castiel, who was born April 13, 1902 and now at the age of twenty. And the youngest member of the family, Anna, who was born February 6, 1905 and was now seventeen.

 

Their mother Eve died in childbirth with Anna, and a year later their father followed her. Zachariah and Michael, who was sixteen, took control of the business. Michael stepped in as a father figure for his siblings. The young Novak’s moved in with their uncle and his children. Castiel and Anna formed a tight bond with their cousins Gabriel and Balthazar. Despite their varied personalities, they were all very close.

 

When the Novak’s first came to America about ten or so years after the gold rush, they somehow got lucky and made a fortune from two things: Gold and oil. They had hit a gold spot, and once they had mined it all up, they hit oil. Their wealth and power doubled tenfold. Christo and Zach had also made wise investments with two very successful businesses: Henry Ford, producer of the Ford cars, and Warner Bros.

 

When Castiel was ten and Anna seven, Michael moved them into their own house and he hired a maid named Missouri to look after them, and still did to this day. Even Michael listened to Missouri. And that is why Castiel was headed to the kitchens, where he was sure the old woman was at. When he rounded the corner, he saw her with flour on her apron and hands. She turned around.

 

“Boy, why aren’t you ready for the gala? Aren’t you leavin’ soon?” she scolded in her slight country twang. Castiel looked at her sheepishly.

 

“I’ve been trying to convince Michael to allow me to stay here.”

 

“I can see why you would do that. Well go get ready while I clean up and then see if I need to fix anything. I will not let you go out into public with an ill fitting attire.” Missouri shooed him out of the kitchen. Castiel trudged up the stairs and into his room. Going to his closet he pulled out some simple black slacks, a white dress shirt, a black jacket, a dark blue tie, and some black dress shoes. Castiel threw off the clothes he was wearing and quickly dressed in his formal clothes. Once he was clothed, he heard Missouri knock on his door.

 

“Come in.” he called.

 

“Alright, let me look at you.” Missouri said and he faced her. After years of doing this Missouri knew what to look for.

 

“You never get that tie right.” Missouri chuckled affectionately at Castiel as she straightened up his tie. They both knew not to attempt to do anything with his hair, it was a lost cause, but that didn’t stop Missouri from complaining about it.

 

“You’re lucky that I don’t have enough time to try to lay it flat.” Missouri said, glaring at his long black hair that stuck up at odd angles.

 

“We both know there is no hope for my hair.” Castiel said with a smile.

 

“Well you need to head downstairs. Your sister is waiting for you.” Missouri patted his cheek and left his room. Castiel closed his eyes with a sigh. The only bright side to going to the gala was that there were at least a few faces to keep him entertained.Castiel jogged down the stairs and found Anna waiting with a smile.

 

Her fiery red hair was done up in intricate curls. Her wine red dress fell down to her ankles and had fluffy sleeves. The smallest black heeled shoes adorned her feet. A matching set of pearl earrings, bracelet, and necklace hung on her. Her thin lips were painted a dark pink and a dark shadow on her eyelids.

 

“Nice of you to join me.” Anna joked as she poked him in the side. Castiel smacked her hand away.

 

“Has Michael already gone?” Castiel questioned as they made their way outside. The early October air was chilly and caused Anna to shiver with goose bumps, yet she declined to going back in to get a coat.

 

“Yes. He left shortly after you left his office.” Anna said. The driver nodded his head in greeting and opened up the car door for them. Anna slid in and Castiel sat next to her, and soon they were off. Conversation was minimum during the ride to the famous Tribune Tower. Four months ago on June 10, the tower was opened. And here many were, on a chilly October 4, going to a gala to recognize Hero’s.

 

Castiel watched the people of Chicago mill around on the streets as dusk closed in. Teenage boys pushed each other around in a small group and worn down mothers dragged their small children in the direction of their home. Love struck couples smiled and laughed in eachothers embrace. People who spotted familiar faces in the streets would nod or wave. Young bachelors scouted the streets for pretty women as potential wives. The elderly walking hunched, bathed in the lights that came to life from the buildings around. Cars grumbled around on the streets while some places had their last customers for the day and other places getting their first for the night. The scene wasn’t new to Castiel, but it still intrigued him. These people had so little, yet he still would see an old man give a boy a nickel, just for him to get a sweet.

 

Castiel found himself for the thousandth time imagining what it would be like if _he_ were a young bachelor laughing and hanging out with his buddies, looking at the faces in the crowd. Or maybe a bartender in one of the bars or clubs, meeting an endless flow of different people. Or one of the new faces, awed by the buildings and signs in a new city, with things to be discovered, and many adventures that could take place. This is why Castiel practically lived in the small library back at their house. The library contained classics; the work of Shakespeare and Dickens and Poe. So many words that would envelope a person and not let you go, because unlike people, books will never leave you, and they will love you from the moment you open them. Castiel was shaken out of his daydream when Anna called his name.

 

“Castiel? We’re here.” Anna said. The driver opened up Castiel’s side of the car. Castiel got out and took his sister’s hand once she was over on his side. Anna linked their arms together. Anna wiggled her eyebrows.

 

“Shall we?” Castiel smiled.

 

“We shall.” he answered as they walked through the doors.

 

Many people were already inside the tower. Tables covered in white cloth with the best china and silverware sat on top with candles in the middle stood organized. There was a small wooden stage where none other that Louis Armstrong and King Oliver stood playing with their Creole Jazz band. The music coming from the various brass and woodwind instruments played a catchy tune that was heard over the dull buzz of chatter. Shoes clacked on the tiled floor. It was full of light and very warm; the air slightly hazed from the smoke of some people’s cigars. Waiters in white carrying silver platters with various foods and drinks. The architecture reminded Castiel slightly of an old catholic church.

 

Then there were the people themselves. Some fit in while others stuck out like a sore thumb. There were men who stood up straight with shoulders back, noses up while they were flaunting their expensive suits and gold plated pocket watches. Their wives were adorned with the finest silks and satins and overwhelming jewelry, with eyes straying to the handsome waiters that would guarantee some scandalous gossip later on. And there were the men that Castiel was sure were the Hero’s. Young, handsome men dressed in Naval uniforms stood with a stiff posture and nervous wandering eyes as they glanced at all the local important people. On their arms were pretty little lady’s who wore their best dresses and jewelry, trying to look impressive as they gazed around with wide awed eyes. As the music switched to an upbeat tune, some of the looser men dragged their ladies out to the small section for the dance floor to dance. The older men stood in a group smoking and laughing heartily at their own jokes while their wives gossiped and judged away. Castiel and Anna almost made it to the middle of it all, when Anna gasped while Castiel was searching the crowd for his cousins faces. Anna dragged him off in some direction.

 

“Jessica? Is that you?” Anna asked a blond who had her back turned. The blond turned around in surprised and lit up once she saw who it was.

 

“Anna! Oh, it’s so good to see you!” Jessica said. Castiel remembered Jessica. Back when they were younger, Jessica and Anna were best friends and damn near inseparable. Even when they had moved the two would ceremoniously write to each other. The two lady’s squealed and hugged each other; delighted. Jess pulled away and smiled at Castiel.

 

“And is this scrawny Castiel?” Jess teased. Castiel made a face but still smiled.

 

“I prefer the term lanky Jess.” he said and took her hand and pulled her into a non-gossip worthy hug. Castiel noticed that there were three men standing off to the side looking rather awkward. They were all wearing cheap black suits, but the tallest one who looked around his age wore one that looked slightly more expensive than the other two. They were all very handsome. The tall one had long brown hair and he was obviously pouting at Jess. He uncomfortably cleared his throat. Jess turned around, like she just remembered that they were there.

 

“Oh, yes. Anna, Castiel, this is my fiance Sam Winchester.” she motioned to the tall one who instantly smiled back at Jess. It was clear as day that they loved each other. “His older brother Dean and Dean’s friend Benny. Guys, this is my best friend Anna Novak and her brother Castiel.” Jessica finished, motioning to the other two. Castiel’s gaze was instantly locked on the brother, Dean. Castiel disregarded looking over the third man.

 

Dean was very handsome and the exact opposite of Castiel. Dean was an inch or so taller than Castiel, with broad shoulders and obvious muscle hidden underneath his suit. His light brown hair was flattened down and went slightly to the side. He had tanned skin and an impossible amount of freckles splashed across his nose and, amazing, cheek bones. But Castiel was drawn to his eyes. They had crinkles around the edges that proved that he smiled quite often. And they were green. An amazing color of green that outstood even an emerald or a lush forest. Dean smiled a crooked, cocky smile that made Castiel’s chest tighten. Castiel had seen many attractive men in his lifetime, but Dean triumphed them all, and would probably continue to do so.

 

Dean leaned forward and stuck out his hand and they shook hands.

 

“Dean Winchester.” he said. His voice was gruff and deep, but not scratchy like Castiel’s.

 

“Castiel Novak.” Once they were done Castiel grudgingly turned his gaze away from Dean and turned to the man beside him.

 

“Benny Lafitte.” the man introduced. He had a faint country twang like Missouri did. Castiel nodded.

 

“Pleasure.” he said. Anna and Jessica were back in a conversation, catching up on all that they had left out of their letters. Castiel touched Anna’s arm to get her attention.

 

“I’m going to for Gabe and Balth and make sure that they aren’t doing anything troublesome.” Castiel explained. Anna nodded.

 

“Okay. Don’t be a stranger.” she said. Castiel kissed her cheek and looked back at the rest of them.

 

“Jess, it was wonderful seeing you again. Gentlemen, it was nice meeting you all.” They shared their goodbyes and Castiel walked off. Maybe this gala wasn’t too bad after all.

 

**Author's Note:**

> Hello my pretties! It is I once more. I thank you for reading this. This story is somewhat historical, with important and known figures from the 1900's. I had to improvise for many things to fit my plot. And feel lucky because I had to do a ton of research to get everything settled and fit together on the correct time lines. Eve is the mother of all, and Christo is the name of God, so ha. The last name Drago come from the  
> Italian word dragon, since dragon's brought Eve to earth. I will not update regularly; I will update wackily. I could post one chapter one day and wait a week to do the next, or write one chapter one day than another the next. I will warn you if you need to know anything. Thank you for reading and read my other works as well. Comment, Kudos, you know the drill! Love you all!!


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